NZ201395A - Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines - Google Patents
Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridinesInfo
- Publication number
- NZ201395A NZ201395A NZ201395A NZ20139582A NZ201395A NZ 201395 A NZ201395 A NZ 201395A NZ 201395 A NZ201395 A NZ 201395A NZ 20139582 A NZ20139582 A NZ 20139582A NZ 201395 A NZ201395 A NZ 201395A
- Authority
- NZ
- New Zealand
- Prior art keywords
- radical
- carbon atoms
- alkyl
- phenyl
- halogen
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 20
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 title claims description 11
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title claims description 9
- -1 B-aminocrotonic acid nitrile Chemical class 0.000 claims description 196
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 171
- 125000004432 carbon atom Chemical group C* 0.000 claims description 116
- 150000001875 compounds Chemical class 0.000 claims description 100
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 99
- 150000003254 radicals Chemical class 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 150000002367 halogens Chemical group 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 65
- 125000001424 substituent group Chemical group 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 125000003545 alkoxy group Chemical group 0.000 claims description 47
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 229920006395 saturated elastomer Polymers 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
- 125000001624 naphthyl group Chemical group 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 24
- 239000003085 diluting agent Substances 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 230000009090 positive inotropic effect Effects 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 150000005840 aryl radicals Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 125000006193 alkinyl group Chemical group 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 230000002829 reductive effect Effects 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002596 lactones Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 239000003826 tablet Substances 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 230000037396 body weight Effects 0.000 claims description 5
- 239000008298 dragée Substances 0.000 claims description 5
- 239000006187 pill Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 150000002081 enamines Chemical class 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 235000000346 sugar Nutrition 0.000 claims description 4
- 239000000829 suppository Substances 0.000 claims description 4
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 230000004941 influx Effects 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 210000004400 mucous membrane Anatomy 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 230000008961 swelling Effects 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 208000029078 coronary artery disease Diseases 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 230000036961 partial effect Effects 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 208000019553 vascular disease Diseases 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 101150009274 nhr-1 gene Proteins 0.000 claims 2
- UQNCXRKGVABEMP-UHFFFAOYSA-N 2,6-dimethyl-5-nitro-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound [O-][N+](=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 UQNCXRKGVABEMP-UHFFFAOYSA-N 0.000 claims 1
- 241000931365 Ampelodesmos mauritanicus Species 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 229910017711 NHRa Inorganic materials 0.000 claims 1
- 229910001424 calcium ion Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ITIJGENTYWNCOC-UHFFFAOYSA-N ethyl 2,6-dimethyl-5-nitro-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C([N+]([O-])=O)C1C1=CC=CC([N+]([O-])=O)=C1 ITIJGENTYWNCOC-UHFFFAOYSA-N 0.000 claims 1
- FRIJQOLHLZPRRS-UHFFFAOYSA-N ethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C([N+]([O-])=O)C1C1=CC=CC(Cl)=C1 FRIJQOLHLZPRRS-UHFFFAOYSA-N 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- ASCGATDWICFABY-UHFFFAOYSA-N methyl 2,6-dimethyl-5-nitro-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C([N+]([O-])=O)C1C1=CC=CC([N+]([O-])=O)=C1 ASCGATDWICFABY-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- DHLMIWQTRTWIJV-UHFFFAOYSA-N propan-2-yl 2-[(2-benzylsulfanylphenyl)methylidene]-3-oxobutanoate Chemical compound CC(C)OC(=O)C(C(C)=O)=CC1=CC=CC=C1SCC1=CC=CC=C1 DHLMIWQTRTWIJV-UHFFFAOYSA-N 0.000 claims 1
- KGFYHTZWPPHNLQ-AWEZNQCLSA-N rivaroxaban Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-AWEZNQCLSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 120
- 230000008018 melting Effects 0.000 description 120
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 76
- 235000019441 ethanol Nutrition 0.000 description 58
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 57
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000000354 decomposition reaction Methods 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 229960004592 isopropanol Drugs 0.000 description 28
- 239000000243 solution Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- QCDJOJKIHZQJGX-UHFFFAOYSA-N 1-nitropropan-2-one Chemical compound CC(=O)C[N+]([O-])=O QCDJOJKIHZQJGX-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- HSPVTPHRQMNTQW-UHFFFAOYSA-N 1-nitroprop-1-en-2-amine Chemical compound CC(N)=C[N+]([O-])=O HSPVTPHRQMNTQW-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- KWLLNBUEXQRJAA-UHFFFAOYSA-N 1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylic acid Chemical compound N1C2=C(CC(=C1)C(=O)O)COC2 KWLLNBUEXQRJAA-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- GSWKJECPHLHZRY-UHFFFAOYSA-N 1,2,3,4-tetrahydrofuro[3,4-b]pyridine-3-carboxylic acid Chemical compound N1C=2C(CC(C1)C(=O)O)=COC=2 GSWKJECPHLHZRY-UHFFFAOYSA-N 0.000 description 5
- QCKSASNKXKHJNS-UHFFFAOYSA-N 4-oxo-5,7-dihydro-1H-furo[3,4-b]pyridine-3-carboxylic acid Chemical compound C1C2=C(CO1)NC=C(C2=O)C(=O)O QCKSASNKXKHJNS-UHFFFAOYSA-N 0.000 description 5
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000004411 aluminium Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 230000008602 contraction Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 4
- MYMKVVIJJCGDIU-UHFFFAOYSA-N 2-benzylthiobenzaldehyde Chemical compound S=CC1=CC=CC=C1CC1=CC=CC=C1 MYMKVVIJJCGDIU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000001427 coherent effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 210000002837 heart atrium Anatomy 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 4
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- PQWXRRYPCWLWEH-UHFFFAOYSA-N methyl 4-(2-benzylsulfanylphenyl)-2-ethyl-5-oxo-4,7-dihydro-1h-furo[3,4-b]pyridine-3-carboxylate Chemical compound C1OC(=O)C2=C1NC(CC)=C(C(=O)OC)C2C1=CC=CC=C1SCC1=CC=CC=C1 PQWXRRYPCWLWEH-UHFFFAOYSA-N 0.000 description 1
- ZAEKQDSVOZXOJS-UHFFFAOYSA-N methyl 4-(2-chloro-5-nitrophenyl)-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C([N+]([O-])=O)C1C1=CC([N+]([O-])=O)=CC=C1Cl ZAEKQDSVOZXOJS-UHFFFAOYSA-N 0.000 description 1
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- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FZXFSARULLKNBK-UHFFFAOYSA-N propan-2-yl 2-methyl-4-(2-methylphenyl)-5-oxo-4,7-dihydro-1h-furo[3,4-b]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC(COC2=O)=C2C1C1=CC=CC=C1C FZXFSARULLKNBK-UHFFFAOYSA-N 0.000 description 1
- IWZBNPRNRWTLBW-UHFFFAOYSA-N propan-2-yl 4-(2-benzylsulfanylphenyl)-2-methyl-5-oxo-4,7-dihydro-1h-furo[3,4-b]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC(COC2=O)=C2C1C1=CC=CC=C1SCC1=CC=CC=C1 IWZBNPRNRWTLBW-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- DLLIQYOCTBBMGB-UHFFFAOYSA-N propyl 2-[(2-benzylsulfanylphenyl)methylidene]-3-oxobutanoate Chemical compound CCCOC(=O)C(C(C)=O)=CC1=CC=CC=C1SCC1=CC=CC=C1 DLLIQYOCTBBMGB-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813130041 DE3130041A1 (de) | 1981-07-30 | 1981-07-30 | Dihydropyridine mit positiv inotroper wirkung, neue verbindungen, ihre verwendung in arzneimitteln und verfahren zu ihrer herstellung |
| DE19823206671 DE3206671A1 (de) | 1982-02-25 | 1982-02-25 | Dihydropyridine mit positiv inotroper wirkung, neue verbindungen, ihre verwendung in arzneimitteln und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ201395A true NZ201395A (en) | 1987-02-20 |
Family
ID=25794943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ201395A NZ201395A (en) | 1981-07-30 | 1982-02-27 | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4532248A (da) |
| EP (1) | EP0071819B2 (da) |
| JP (2) | JPH066535B2 (da) |
| KR (2) | KR890001567B1 (da) |
| AU (1) | AU566502B2 (da) |
| CA (1) | CA1212672A (da) |
| CH (1) | CH656530A5 (da) |
| DE (1) | DE3276112D1 (da) |
| DK (1) | DK339782A (da) |
| ES (1) | ES514525A0 (da) |
| FI (1) | FI822643L (da) |
| FR (1) | FR2511247B1 (da) |
| GB (1) | GB2105989B (da) |
| HK (1) | HK19389A (da) |
| IE (1) | IE54259B1 (da) |
| IL (1) | IL66405A (da) |
| IT (1) | IT1190929B (da) |
| NL (1) | NL8202958A (da) |
| NZ (1) | NZ201395A (da) |
| PH (1) | PH23086A (da) |
| SG (1) | SG52988G (da) |
Families Citing this family (141)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2111978B (en) * | 1981-10-19 | 1985-05-01 | Maruko Pharmaceutical Co | 1 4-dihydropyridine compounds |
| DE3269219D1 (en) * | 1981-11-17 | 1986-03-27 | Fisons Plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
| DE3207982A1 (de) * | 1982-03-05 | 1983-09-08 | Bayer Ag, 5090 Leverkusen | Neue 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihrer verwendung in arzneimitteln |
| DE3209274A1 (de) * | 1982-03-13 | 1983-09-15 | Bayer Ag, 5090 Leverkusen | Pyridincarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4414213A (en) * | 1982-03-22 | 1983-11-08 | Mead Johnson & Company | Dihydropyridyl cyclic imidate esters and their pharmaceutical use |
| EP0100189B1 (en) * | 1982-07-22 | 1986-05-28 | Pfizer Limited | Dihydropyridine anti-ischaemic and antihypertensive agents |
| DE3235221A1 (de) * | 1982-09-23 | 1984-03-29 | Bayer Ag, 5090 Leverkusen | Ringverbrueckte 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| EP0106275B1 (en) * | 1982-10-15 | 1991-03-13 | Kyowa Hakko Kogyo Co., Ltd. | 1,4-dihydropyridine derivatives |
| JPS5970666A (ja) * | 1982-10-15 | 1984-04-21 | Kyowa Hakko Kogyo Co Ltd | １，４−ジヒドロピリジン誘導体 |
| US4656181A (en) * | 1982-11-24 | 1987-04-07 | Cermol S.A. | Esters of 1,4-dihydropyridines, processes for the preparation of the new esters, and medicaments containing the same |
| EP0111455A3 (de) * | 1982-12-10 | 1984-07-25 | Ciba-Geigy Ag | Ungesättigte Lactone |
| EP0111453A1 (de) * | 1982-12-10 | 1984-06-20 | Ciba-Geigy Ag | Amid-Verbindungen |
| GR79111B (da) * | 1982-12-20 | 1984-10-02 | Lepetit Spa | |
| DE3311003A1 (de) * | 1983-03-25 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Chromon- und thiochromonsubstituierte 1,4-dihydropyridinlactone, mehrere verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| EP0125803A3 (en) * | 1983-04-27 | 1987-01-21 | FISONS plc | Pharmaceutically active dihydropyridines |
| DE3319956A1 (de) * | 1983-06-01 | 1984-12-06 | Bayer Ag, 5090 Leverkusen | 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| US4568677A (en) * | 1983-07-23 | 1986-02-04 | Pfizer Inc. | 2-(4-Pyrimidone alkoxyalkyl) dihydropyridine anti-ischaemic and antihypertensive agents |
| EP0141221A1 (en) * | 1983-09-26 | 1985-05-15 | Nissan Chemical Industries Ltd. | 1,4-Dihydropyridine-5-phosphonic acid ester |
| CA1339372C (en) * | 1983-09-26 | 1997-08-26 | Nissan Chemical Industries Ltd. | Dihydropyridine-5-phosphonic acid cyclic ester |
| FR2554109A1 (fr) * | 1983-11-01 | 1985-05-03 | Sandoz Sa | Nouveaux derives de la 1,4-dihydropyridine, leur preparation et leur utilisation en therapeutique comme medicaments |
| JPS60120861A (ja) * | 1983-12-02 | 1985-06-28 | Otsuka Pharmaceut Co Ltd | ジヒドロピリジン誘導体 |
| US5137889A (en) * | 1983-12-02 | 1992-08-11 | Otsuka Pharmaceutical Co., Ltd. | Dihydropyridine derivatives and process for preparing the same |
| DE3343658A1 (de) * | 1983-12-02 | 1985-06-13 | Bayer Ag, 5090 Leverkusen | Hydroxy-tetrahydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| JPS60156671A (ja) * | 1984-01-25 | 1985-08-16 | Yamanouchi Pharmaceut Co Ltd | ジヒドロピリジン誘導体およびその製造法 |
| GB8403866D0 (en) * | 1984-02-14 | 1984-03-21 | Recordati Chem Pharm | Diphenylalkylaminoalkyl esters |
| DE3410645A1 (de) * | 1984-03-23 | 1985-09-26 | Bayer Ag, 5090 Leverkusen | L-alkylsubstituierte 1,4-dihydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| IE57810B1 (en) * | 1984-03-27 | 1993-04-21 | Delagrange Lab | 1,4-dihydropyridine derivatives,their preparation and their use |
| US4567268A (en) * | 1984-04-03 | 1986-01-28 | Merck & Co., Inc. | Process for preparation of certain tetrahydrofuro[3,4-b]pyridines |
| DE3414801A1 (de) * | 1984-04-19 | 1985-10-24 | Bayer Ag, 5090 Leverkusen | 4-(nitrophenyl)-tetrahydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4672068A (en) * | 1984-05-04 | 1987-06-09 | Fujirebio Kabushiki Kaisha | Antihypertensive 1,4-dihydropyridines having a conjugated ester |
| GB8412208D0 (en) * | 1984-05-12 | 1984-06-20 | Pfizer Ltd | Quinolone inotropic agents |
| DE3420784A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 3-nitro-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| GB8415386D0 (en) * | 1984-06-15 | 1984-07-18 | Pfizer Ltd | Therapeutic agents |
| US4731370A (en) * | 1984-06-25 | 1988-03-15 | Toyama Chemical Co., Ltd. | Pyridyl ester containing 1,4-dihydropyridine derivatives and salts thereof and pharmaceutical composition containing the same |
| GB2162513B (en) * | 1984-06-25 | 1988-01-20 | Toyama Chemical Co Ltd | Dihydropyridine derivatives |
| FI852359L (fi) * | 1984-06-27 | 1985-12-28 | Hoffmann La Roche | Dihydropyridinderivat. |
| JPS6112662A (ja) * | 1984-06-28 | 1986-01-21 | Yamanouchi Pharmaceut Co Ltd | ジヒドロピリジン誘導体及びその製法 |
| GB8421039D0 (en) * | 1984-08-17 | 1984-09-19 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| NZ212895A (en) * | 1984-08-22 | 1988-07-28 | Glaxo Spa | 1,4-dihydropyridine derivatives and pharmaceutical compositions |
| DE3431152A1 (de) * | 1984-08-24 | 1986-03-06 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung optisch aktiver, substituierter 1,4-dihydropyridine und ihre verwendung als arzneimittel |
| ATE107284T1 (de) * | 1984-09-28 | 1994-07-15 | Byk Gulden Lomberg Chem Fab | Neue diarylverbindungen. |
| JPS6191185A (ja) * | 1984-10-11 | 1986-05-09 | Sumitomo Seiyaku Kk | 新規なオキサジアゾリル−１，４−ジヒドロピリジン誘導体 |
| US4994476A (en) * | 1984-10-31 | 1991-02-19 | Bristol-Myers Company | Dihydropyridin-3,5-dicarboxylates incorporating aryloxypropanolamine moieties |
| US4616002A (en) * | 1984-11-09 | 1986-10-07 | Ciba-Geigy Corporation | Dihydro pyridine compounds, compositions and use |
| DE3443179A1 (de) * | 1984-11-27 | 1986-05-28 | Cassella Ag, 6000 Frankfurt | 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung |
| US4678796A (en) * | 1984-11-30 | 1987-07-07 | Warner-Lambert Company | 2-alkylidene derivatives of 1,2,3,4-tetrahydropyridine-2,5-pyridine carboxylic acid dialkyl esters useful for treatment of cardiovascular disorders |
| HUT39179A (en) * | 1984-12-10 | 1986-08-28 | Sandoz Ag | Process for production of derivatives of 1,4-dihydro-piridin |
| JPH0676405B2 (ja) * | 1986-06-13 | 1994-09-28 | 日清製粉株式会社 | １，４―ジヒドロピリジン誘導体およびそれを含有する医薬組成物 |
| DE3447169A1 (de) * | 1984-12-22 | 1986-07-03 | Bayer Ag, 5090 Leverkusen | Optisch aktive nitrodihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
| DE3501855A1 (de) * | 1985-01-22 | 1986-07-24 | Bayer Ag, 5090 Leverkusen | 5-aryl-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| US4652573A (en) * | 1985-03-14 | 1987-03-24 | Nelson Research & Development Co. | Calcium antagonist N-hetero ester 1,4-dihydropyridines |
| US4833150A (en) * | 1985-03-14 | 1989-05-23 | Nelson Research & Development Co. | 1,4-dihydropyridines |
| DE3686185T2 (de) * | 1985-03-15 | 1993-01-14 | Suntory Ltd | N-substituierte 3,4-dihydropyrimidinderivate, verfahren zu deren herstellung und diese enthaltende zusammenstellung fuer die behandlung von anordnungen eines kardiovascularen systems. |
| DE3517473A1 (de) * | 1985-05-15 | 1986-11-20 | Bayer Ag, 5090 Leverkusen | Pyrimidinyl-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
| US4728652A (en) * | 1985-05-20 | 1988-03-01 | E. R. Squibb & Sons, Inc. | 2-substituted thio or oxy-4-aryl or heterocyclo-5-carboxy-1,4-dihydropyrimidines, composition containing them, and method of using them to reduce blood pressure |
| CA1267416A (en) * | 1985-06-17 | 1990-04-03 | Ila Sircar | 1,4-dihydropyridine derivatives useful for the treatment of cardiovascular disorders |
| DE3521761A1 (de) * | 1985-06-19 | 1987-01-02 | Bayer Ag | Neue 1,4-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
| ZA863578B (en) * | 1985-06-21 | 1987-02-25 | Hoffmann La Roche | Dihydropyridine derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1923990C3 (de) * | 1969-05-10 | 1978-11-23 | Bayer Ag | Verfahren zur Herstellung von N-substituierten M-Dihydropyridin-S.S-dicarbonsäureestern |
| US3932645A (en) * | 1971-04-10 | 1976-01-13 | Farbenfabriken Bayer Ag | Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acid |
| DE2117571C3 (de) * | 1971-04-10 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1,4-Dihydropyridin-33-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2218644C3 (de) * | 1972-04-18 | 1982-08-19 | Bayer Ag, 5090 Leverkusen | Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| JPS4935277A (da) * | 1972-08-07 | 1974-04-01 | ||
| DE2242786A1 (de) * | 1972-08-31 | 1974-03-14 | Bayer Ag | Verfahren zur herstellung von neuen 2-amino-1,4-dihydropyridinen mit einer carbonylfunktion sowie ihre verwendung als arzneimittel |
| GB1552911A (en) * | 1975-07-02 | 1979-09-19 | Fujisawa Pharmaceutical Co | 1,4 dihydropyridine derivatives and the preparation thereof |
| DD122524A1 (da) * | 1975-10-17 | 1976-10-12 | ||
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| DE2659665A1 (de) * | 1976-12-30 | 1978-07-13 | Nattermann A & Cie | Neue 1,4-dihydropyridin-derivate |
| DE2752820A1 (de) * | 1977-11-26 | 1979-05-31 | Bayer Ag | Neue nitrosubstituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| NO780094L (no) * | 1978-01-11 | 1979-05-21 | Finn Hallingstad | Fremgangsmåte ved fremstilling av fôr for fôring av fisk i saltvann |
| CA1110234A (en) * | 1978-01-18 | 1981-10-06 | Hoffmann-La Roche Limited | 4-pyridone-3-carboxylic acids and process for the preparation thereof |
| JPS5527054A (en) * | 1978-08-15 | 1980-02-26 | Gen Foods Corp | Adsorption method |
| US4285955A (en) * | 1978-10-31 | 1981-08-25 | Bayer Aktiengesellschaft | 1,4-Dihydropyridinecarboxylic acids |
| DE2847237A1 (de) * | 1978-10-31 | 1980-05-14 | Bayer Ag | Verfahren zur herstellung von 1,4-dihydropyridincarbonsaeuren sowie ihre verwendung als arzneimittel |
| DE2935451A1 (de) * | 1979-09-01 | 1981-03-19 | Bayer Ag, 5090 Leverkusen | Optisch aktive 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arneimittel |
-
1982
- 1982-02-27 NZ NZ201395A patent/NZ201395A/en unknown
- 1982-07-13 AU AU85945/82A patent/AU566502B2/en not_active Ceased
- 1982-07-14 US US06/398,034 patent/US4532248A/en not_active Expired - Lifetime
- 1982-07-20 DE DE8282106537T patent/DE3276112D1/de not_active Expired
- 1982-07-20 EP EP82106537A patent/EP0071819B2/de not_active Expired - Lifetime
- 1982-07-22 NL NL8202958A patent/NL8202958A/nl not_active Application Discontinuation
- 1982-07-27 IL IL66405A patent/IL66405A/xx not_active IP Right Cessation
- 1982-07-27 CH CH4566/82A patent/CH656530A5/de not_active IP Right Cessation
- 1982-07-28 FI FI822643A patent/FI822643L/fi not_active Application Discontinuation
- 1982-07-28 IT IT22620/82A patent/IT1190929B/it active
- 1982-07-29 PH PH27645A patent/PH23086A/en unknown
- 1982-07-29 CA CA000408355A patent/CA1212672A/en not_active Expired
- 1982-07-29 FR FR8213257A patent/FR2511247B1/fr not_active Expired
- 1982-07-29 GB GB08221931A patent/GB2105989B/en not_active Expired
- 1982-07-29 ES ES514525A patent/ES514525A0/es active Granted
- 1982-07-29 DK DK339782A patent/DK339782A/da not_active Application Discontinuation
- 1982-07-29 IE IE1827/82A patent/IE54259B1/en not_active IP Right Cessation
- 1982-07-30 JP JP57132344A patent/JPH066535B2/ja not_active Expired - Lifetime
- 1982-07-30 KR KR1019890001597D patent/KR890001567B1/ko active
- 1982-07-30 KR KR8203412A patent/KR890001566B1/ko active
-
1988
- 1988-04-22 SG SG52988A patent/SG52988G/en unknown
-
1989
- 1989-03-09 HK HK193/89A patent/HK19389A/xx not_active IP Right Cessation
-
1992
- 1992-12-16 JP JP4354673A patent/JPH05271078A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1190929B (it) | 1988-02-24 |
| KR890001566B1 (ko) | 1989-05-08 |
| FR2511247B1 (fr) | 1986-03-07 |
| EP0071819B2 (de) | 1992-06-10 |
| DK339782A (da) | 1983-01-31 |
| HK19389A (en) | 1989-03-17 |
| IL66405A0 (en) | 1982-11-30 |
| IT8222620A1 (it) | 1984-01-28 |
| KR890001567B1 (ko) | 1989-05-08 |
| CA1212672A (en) | 1986-10-14 |
| PH23086A (en) | 1989-04-10 |
| JPS5826872A (ja) | 1983-02-17 |
| EP0071819A1 (de) | 1983-02-16 |
| DE3276112D1 (en) | 1987-05-27 |
| GB2105989A (en) | 1983-04-07 |
| IT8222620A0 (it) | 1982-07-28 |
| IE821827L (en) | 1983-01-30 |
| ES8305716A1 (es) | 1983-04-16 |
| GB2105989B (en) | 1986-01-08 |
| SG52988G (en) | 1993-02-19 |
| ES514525A0 (es) | 1983-04-16 |
| EP0071819B1 (de) | 1987-04-22 |
| IE54259B1 (en) | 1989-08-02 |
| NL8202958A (nl) | 1983-02-16 |
| US4532248A (en) | 1985-07-30 |
| JPH066535B2 (ja) | 1994-01-26 |
| JPH05271078A (ja) | 1993-10-19 |
| AU566502B2 (en) | 1987-10-22 |
| CH656530A5 (de) | 1986-07-15 |
| FR2511247A1 (fr) | 1983-02-18 |
| KR840000494A (ko) | 1984-02-22 |
| FI822643L (fi) | 1983-02-01 |
| AU8594582A (en) | 1983-02-03 |
| IL66405A (en) | 1987-12-31 |
| FI822643A0 (fi) | 1982-07-28 |
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